Three hires to make sooner than you’d think
Disclaimer: While this post was written in 2026, it neither focuses on AI nor invokes anything generative in its drafting or editing. Any slop is 100% human-derived.
There are many key inflection points that successful startups navigate. And one of the most difficult is the shift away from being hyper-lean: From day one, you’ve built as a team of six engineers plus one founder who manages sales and everything else. But as you realize product success, paying customers, and additional rounds of funding, it is not only OK but absolutely necessary to add specialist talent.
Most teams wait too long to do so.
Here are three roles that are worth hiring for before something breaks:
Head of Finance: after your Series A
You, as a founder, are a force of nature and brilliant enough to tackle most challenges through first-principles thinking. But “modern” finance and accounting are over 500 years old, and there are accrued practices that your company needs to apply correctly, now.
Here are a few key areas that often fall short without an experienced finance lead:
- Instrumenting your business, including market-standard application of key metrics. Gross margin is probably the most commonly misapplied—for instance, how much of your engineer’s time belongs in COGS?
- Cash management with accuracy and precision to project cash runway under a range of operating scenarios.
- Support for fundraising. Series B is often the most difficult round to raise; investors at this stage are looking everywhere for signal that you are ready for accelerated scaling. This applies to your financial rigor and even the robustness of your financial model.
Head of Security: after Series B
More accurately, as soon as your customers trust that you will not lose or leak customer data. I.e., pretty damn early.
This hire is one that is soooo easy to put off. You and your awesome dev team know that there is nothing more critical than delivering value, so you absolutely must start there. And you’ve thought about security since the start and have absolutely covered the big risks. So the odds of an edge case hurting your company seem exceedingly small—likely 1% or lower.
The reality is that while all of the above calculus feels right, it hugely underestimates the accumulated risk of i) the sheer number of edge cases and ii) the fact that every new commit to prod or even just update to cloud service configs represents another roll of the dice. In other words:
P(negative security event) = 1% * (# of edge cases) * (# of changes to prod)
We’ve seen multiple fantastically successful companies only realize this math after customer data leaks or systems go down. Either one of those events costs your company far more than hiring a security lead.
The objectively “correct” move is to hire early.
Here are a couple of hacks that I’ve found can help if you agree with the (T)hinking part of all this but just can’t get there on the (F)eeling front:
Look for someone who can own security end-to-end for a stretch, before later specializing. This means covering:
- Security of your product
- Compliance (e.g., SOC2, etc.)
- Secure use, including configuration of cloud services, endpoints, etc
Include a slide in the appendix of each board deck covering security incidents, resolutions, and next steps (including ways to mitigate the risk of repeat incidents). This slide shows that security matters to you as a team and justifies the spend on the additional headcount. More importantly, it establishes momentum on the classic “you can’t improve what you don’t measure” front.
Executive Assistant: around your Series C. Hell, even earlier if you’re willing.
Ok, this may be the hardest one to convince you of. You have demonstrated through personal scrappiness and leadership by example that you are not above any task and that doing a ton with very little is the linchpin to your company’s culture.
The issue is that, around the Series C, you are transitioning from a product visionary to a scale-up CEO. And that means you have to perform against the core elements of your role many more times per week (e.g., meet with customers) while also developing new skills (organizational management, public speaking, acquisitions, etc.).
So it’s time to delegate certain tasks while concentrating on honing others. And it is wrong to think of an EA as pure leverage. They are focused specialists who are just flat-out better at what they do than you are.
E-mountain bikes are a perfect analogy: before you experience one, the mere concept feels like cheating; an affront to the sport. But trust me, you are approaching a hill climb that is difficult enough that you will need the assist. Don’t wait until you are bonking mid-way up to make the move to team up with a great EA.
Conclusion
There’s a well-known business book titled “What Got You Here Won’t Get You There.” I’ve never read it but have always liked the title. You have moved mountains to create escape velocity for something special. Consider making key hires like the ones above before they feel natural. You won’t get every one “right” but these uncomfortable acts of re-tooling are absolutely required for your long term success.
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